Organic Chemistry II Biological Emphasis
Organic Chemistry II Biological Emphasis CHEM 3153
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This 68 page Class Notes was uploaded by Wyatt Braun on Monday October 26, 2015. The Class Notes belongs to CHEM 3153 at University of Oklahoma taught by Mark Morvant in Fall. Since its upload, it has received 12 views. For similar materials see /class/229272/chem-3153-university-of-oklahoma in Chemistry and Biochemistry at University of Oklahoma.
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Date Created: 10/26/15
Practice 1 Using the following IR did the following reaction go to completion OH ResinCrOSH O W gt W M If Ak Alf Filer M HI I ll 0 l I I I I 100 3003 EDD 151m 0930 KRVENUHEER vnl TRHHSHITTNNCEI 39439 Using the following IR did the following reaction go to completion W0 Ethanol ltO gt OH H OCHZCHs DD m U I rnnusmrrnucam I F 1000 SKID HRVENUHE ERI II 58 5 5 Practice 2 Match the following moleculis witht ego ect 1H NMR below W OH I WOH 4 6 C a A g A 5 c o f 22 z 3 l 39 J 14 J i 32 1221 I I fC 6 F I OH j m A 7 I I 1 I I I l l I I I l I I l I l I I 11 10 9 8 7 6 5 4 3 Z 1 HSP DD 002 ppm J L lU f 5 m 6 I 39 l l l 39 l 39 I 39 39 l I I WW 1 l 11 10 9 8 3quot 6 5 4 3 2 1 O H3P03S74 all 10 9 HPf lleZli Practice 3 Use the following spectra to propose a structure for the sample Sample 1 C9H1002 DD TE HHS TTHNE E Z1 m o w 1 z JED 3000 l I 200B 1 HRVENUHE ERI ul 0 9 l 5 c a x I 1000 I an Q0 Sample 2 C4H100 ppm 12 q J4 my I quot66 Z of I 839 MW 5 Exsm Nsmc 1 thch of the fonowmg compounds 1s sn sm1dcv 1 CH3CHZNHZ vs HOCCHZNHJ II o 11 CIIgNHNH2 v H CH1 CN HZ 0 A x a u swc Sscnon 157 1 2 thch of the fonowmg compounds 1s sn acyl chxondsv Cl Q A x a 11 Answer E Sscnon 157 1 c m OCHzCl IV 1 cx cl v cup 5 m 3 thch of the fouowmg compounds 1s sn ester V 15 O i ascnon 157 1 CH3COOH caicocca3 c m D W D W D xv 4 Which of the following compounds is an anhydride 3 0 I 1 0 1V H L39HB UD J CH3000H o 39quot 0 0 m n V II II CH3C lt c J CHSCOCCHg O l I ll CH3COH A I B H C III D IV Answer E Section 1671 5 What is the common name for the following compound 0 CH3CHCH2COH Cl A A chlorobutyric acid B A chlorobutanoic acid C B chlorobutanoic acid D B chlorobutyric acid E 3 chlorobutyric acid Answer D Section 1671 6 What is the IUPAC name for the following compound CH3 CH3CH2CHCH2COOH A 3 methylvaleric acid B isohexanoic acid C B methylvaleric acid D 2 methylpentanoic acid E 3 methylpentanoic acid Answer E S ection 1 6 r 1 EV Q 5 Q 7 Which of the following compounds is benzoyl chloride L G Cl IV ijJKCOG VikiCl OCHECI quot1 f quotM 5 coocm V R gg A I B 1 C III D IV Answer D Section 1 6 7 1 8 What is the common name for the following compound 0 O HC O CH A diformyl ether B formyl formate C ethanoic anhydride D formic anhydride E propanoic anhydride Answer D Section 1 6 r 1 9 What is the IUPAC name for the following compound ll If K CH3COCH3 k V I A methyl phenylacetate B benzyl methylacetate C methyl benzoate D phenyl acetate E benzyl acetate Answer E Section 1 6 r 1 EV 9 8 W 10 Which of the following compounds is methyl formate A O H HCOOCH3 B O CH3COCH3 E Q CH3COH Answer B Section 16 r 1 11 Which of the following compounds is A butyrolactone o 11 I IV to o r J CH3 xx i O 11 E 0 V o sf a CH 3 0 D1 O A1 BH CHI Dn7 Answer C Section 16 r 1 EV 12 What is the common name for the following compound V O C NI Iz A phenylcarbamxde E benzamxde nswer E Sachem 157 1 de 13 thch of the followxng compounds 5 NNrdxmethylbenzamxde7 E N39HCH 3 IV 0 n CNH V CH O H CH3 C CH3 aquot cjm o CIIg JJN39HCHg C pH CN CH3 D W 14 What Is the epmmpn name for the following compound7 14 O A benzenecyanxde CN benzonnnle Seensn 157 1 15 thch pr the rpnpwrng epmppunes rs Aevalerolactam39V 15 o o 1 K 0 IV E N L CH3 0 CHI 0 1 i A x a u C m D W E v Answer D Seensn 154 SHORT ANSWER is prpvree the prpper mm nsme for the epmppune below is COZCHKCH92 Answer lsopropyl cyclohexanecarboxylate Seensn 1571 17 Prevrde the prpper IUPAC name for CICH2CH2CONHCH3 17 wer Nemecnyleaeemprpprppsnsmrde 1571 Seensn 13 Provroe the proper IUPAC nsrne for the eornoound below CHSCHE H E H C zc gc gcocl Answer tnvlerroctenoyl enxonoe Seenon 157 1 19 Provroe the structure of oroosnore anhydnde Answer CH3CH2CO20 1571 Seenon 20 Answer 255eerrrnecnyxnemnennrue 571 Seenon 21 Provroe the IUPAC nsrne for the organ compound below COZH cw wer Aeenxoroesernecnyxnemnore and Seenon 157 1 22 Provroe the IUPAC nsrne for the organ compound below 0 Answer 1soorooy1 butanoate 1 Seenon 157 23 Provroe the IUPAC nsrne for the organ compound below 3 0 Answer pentanoyl enxorrde 1571 Seenon 24 Prde the syseemm mm a the pm Shawn belaw o OCH A Mom CH3 0 we ehyrarmewpemme denvihves A 5p2tetrahednl a 5 an phm csp2 ngan21phmr D Spa e rmam 2 5p mg phm Answer 2 bar Answer snow ANSWER 27 wmh 7 mex beluwxs 51mm m m 51mm i CH FlCH CH3 H humane tarbmyl Ewes CrN band 1pm dauble band hzrat ar 23 thch of the fonowmg compounds has the lowest bmhng polnt7 A butane and Sachem 1573 SHORT ANSWER 29 29 0 NKOH OH III we I lt x lt m 1573 Sachem 30 p k M and demame does pipenne belong V O N A cro E no C fcro 10647 E quotno nswer Sachem 1575 reads Nth cbgcocl tufurm mummy A nswer c 33 m mumpme w Substxmtxun mes erh r ya 2 yd El 55 puma bydepmmmnm C7 in 5N2 mum mm D his a the 19mg gmup 5 mums by mmnggmem a the irbxinm SHORT ANSWER Write the word or phrase that best completes each statement or answers the question 34 Do you expect the following reaction to go to completion Why or why not 34 O R c OCH3 NaCl e Answer No The equilibrium will favor the reactants because the nucleophile Cl is a much weaker base than the leaving group CH30 Section 1 6 r 5 MULTIPLE CHOICE Choose the one alternative that best completes the statement or answers the question 35 Which of the following compounds is most reactive toward nucleophilic acyl substitution 35 A O O R C OC R B O R COH C O R c OCH3 D O R C NH2 E O R C Cl Answer E Section 1 6 7 6 36 Which of the following compounds is the least reactive toward nucleophilic acyl substitution A O H R C NH2 B O H R C OH C O 0 II II R C O CR D 0 R c OCH3 E O R C Cl AnswerA Section 1 6 7 6 37 Which of the following compounds is hydrolyzed most rapidly inaqueous NaOH A O H R c OCH3 B O H R C OH C O O H R C o c R D 0 ll R C Cl E O H R C NH2 Answer D Section 1 6 r 6 3m 38 Which of the following compounds is hydrolyzed rnost slowly in aqueous NaOH 38 A O 0 R g O g CH3 B 0 R g NH2 C R C 0 CH Q D 17 R C 0 CH3 E O R g Cl Answer B Section 1 6 r 6 39 Acetyl chloride undergoes nucleophilic substitution at a faster rate than methyl acetate 39 because A esters hydrolyze faster than acid chlorides B the ester is more sterically hindered than the acid chloride C chloride is a better leaving group than methoxide D the acid chloride is more sterically hindered than the ester E the methoxide is a better leaving group than chloride Answer C Section 1 6 r 6 40 Typically arnides will hydrolyze under 777777 conditions than esters 40 A more dilute B less vigorous C milder D rnore saline E more vigorous Answer E Section 1 6 r 6 SHORT ANSWER Write the word or phrase that best completes each statement or answers the question 41 List the following carboxylic acid derivatives in decreasing order of reactivity in 41 nucleophilic acyl substitution reactions acetic anhydride methyl acetate acetarnide acetyl chloride Answer acetyl chloride gt acetic anhydride gt methyl acetate gt acetarnide Section 1 6 r 6 MULTIPLE CHOICE Choose the one alternative that best completes the statement or answers the question 42 Which of the following is the best method for preparing 42 O l CH3 COCH3 A 0 H CH3C H CH3OH 9 B O 9 CH3C NH2 CH3ONa 9 C O 9 ea CH3 C H CH3ONa 9 D O Q H CH3 C OH CH3OH E 0 9 lt9 CH3 C c1 CH3ONa E Answer E Section 1 6 r 8 43 Esters and amides are most easily made by nucleophilic acyl substitution reactions on 43 A acid anhydrides B carboxylates C carboxylic acids D alcohols E acid chlorides Answer E Section 1678 44 Which of the following compounds would yield acetic acid when hydrolyzed under heat A O H CH 3 c C1 B CH3CEN C O CH 3 c OCH3 D O O H H CH3C O CCH3 E all the above Answer E Section 1 6 r 8 SHORT ANSWER Write the word or phrase that best completes each statement or answers the question 45 What are the products from the following reaction 45 O quot c1 OH Answer 1 C O HCl V Section 1678 46 Provide a detailed stepwise mechanism for the reaction of acetyl chloride Mth 46 methanol to produce methyl acetate and HCl Answer Cl 4 fa o oi o H H 1 1 m HI a CHB C Cl CH3 9H l CHg CCl 1 CH3 c OCHi kn 39 I CH3 0 H 4 HCl CH3 C OCH3 Section 1678 Answer ca3cnfccl mg pcmcazeiwlacagcngecim H NH7 39 1 HCl r CH3CH3 1km CH Cm V Seetrsn 1575 Aajv m 1h wrtn twe equwsxents of tnethylamlne Wes the student successful39V Expxsrn Answer No esrbenyx Tne resetren would have proved successful nsd dretnyxsrnrne been sed Seetrsn ma Answer tnereby render n nonnucleophxhc Seetrsn ma 50 Prevrde the major ergsnre preduet of the followxng NaOZFCHz Clock Seetrsn 1575 Answer 51 Prevrde the major ergsnre preduet erthe followxng cow HZC HZCHZOH Answer 002chch3 Seeusn we 52 Prevrde the major ergsnre preduet of the resetren below 01 Answer 1 H200 2 socnz pyr a CH30I422NH x5 NCHZCH32 Seetrsn 1575 53 Whreh of the renewrng rs the best rnethed for prepsnng ssprnn COOH 1 occm 1 COOH d N COOH r EH a 011 11 0C 3 r 47NH2 a CH V COOH He 3 HCOOH CI hCiOiCCHg gt COOH 0H CH3C a D o H out A x a u c m D xv Answer E Seetrsn 1579 EJV SHORT ANSWER 54 What 5 the product of the following reactmn V 54 H10 0 Answer 1 07011 l his is me hydrolysis ofan Q anhydride to an acid io 0 555m 157 55 55 phem Answer 4 0 H n cagc z c o C 032m IIo igt 3017 c q V 0 OCCH2CH1 K o H o H 1 H lt cameos Jgiccnzc g CH3CH2C02H c gcnzcozph 555m 15 5e 55 reads wnh 1 equmxem a meannng n a are and and memyx formats 555m 5 57 thch 57 Emma A sumo 13 b mm c Niethylbutanamxde D both A and c E both E and c nswer D Secuun 154a as wnren of the renewrne esgers undergoes nydrexysrs rn base rnes essuyv A cmcmcozcm a CeHstCCHS C cmncmmcozcm D pemoxsmoxcm E pecchEmozccHs swer D Seenen m m SHORT ANSWER 59 Prevrde the major organ product enne resenen below 0 0 CHsCHZOH 4 Hca1 Answer HOCH2CH2CH2CH2C02CH2CH3 Seenen m m an Q 3 NH Answer 0 0 me gA r 2 as Seenen m m m prevrde the rnsJer ergsnre product of the following COZCH3 1H3CHZ4N39H2 excess Answer N W H Seenen m m I L MULTIPLE CHOICE Choose the one alternative that best I the t t or the question 62Vth iofthefoHovdngisoneofthestepsintheinechanmnnofthefo omdngreac on 62 0 0 H H H R C OH CH3OH 9 R C OCH3 H2O A O H OH H R C OH CH30H R C OH H O CH3 43 9 B O O H H 9 R C OH CH3OH 9 R c OH C 9 9 0 H OH I e R C OH CH3O RCOH OCH3 D 9 O O R C OH CH3OH 9 R C OH HOCH3 E O 0 ll 9 R C OH CH3O R c OH I OCH3 Answer A Section 16 7 1 1 21 63 wnren t A s carboxylate snren E 1eprepsne1 C s pretensted carbonyl D s esrbsnre E s esrbeestren Answer E Seetrsn 1m 11 snom ANSWER 64 ethyl seetste wnh reprepsnex Answer fe 041 H CH carcion nicngicVJto 40H 1 41 OH H OH H lt1 1 H 1 CHECEQOE C gicsorr C r c on lt c rgiom 4 H Free 07m 1 carciopr Seetrsn 1541 65 as Prevrde the major organ preduet of the reacnon below 010 Answer NaOH H20 7CHZCH3 0 x5 CchHZCOfNa39 02N0 Na39 Seetrsn 1m 12 methyl benzeste wrtn sedmrn ethoxxde Answer Q 0 o a Og DEL 1 oMc 1 7051 EOMe s 6 C Q Y Seetrsn 157 12 CE s7 Vvhzt 5 the pram Emma gram the fullmngreitum cioH a 12 H CHgoH 4 7 O o E 12 707011 5 Eiong I H20 IV H20 12 o O Q 5 CH 5 H W 7 7 3 H H20 V C40 CH3 5 H20 2 O m 407CH3 20 m cm W m Answer D nswer c 59 Vvhzt 15 the m m9 pmm a the fullmng mm 00011 He Z g 110011chon 4 7 L CHZCH2 COOH HOOC 11 cHcHocoo11 HOOC Cd C 111 c CH20H20 o H CH IV cocHchzoa 19 C1 V cicg 700Hchon A 1 a 11 c 111 D1v Answer D awards 25m gamma Aadd1t1m 3 Wm m meens 1215 funn a 5mm 13 e 2 Man 3 mm 1 and as a atalyst Emma Answer 2 SHORT ANSWER 71 Gwe a 39 v a methanol Am A H W Q CH3 C OH 11 1 CH3 C OH cazon c1137 W Hgo CH3COCH3 Seem 1545 0 11 C70H 72 thch of the fenewmg methods can be used to prepare 3 N7 A CH3CH2CEN e 32 a a CH3Er ec N A C CH3CH2Er e NH3 4 E E and c Answer E Seeuen 15715 73 H must be A secondary a Nemethylated E ternary swer c Sachem 157 1 me amide 73 prepaneate A propyl benzeate E ne reaetren r E Seetran 1545 SHORT ANSWER 75 Prevrde the major erganre preduet ofthe followxng o socl2 Answer Seetran me 1 76 What reagents are used ta dehydrate arnrdes ta nnnles39V Answer P205 or P003 Seetran me 1 77 amldes r Answer fearernernbered nng Seenan 15717 78 Provide the major organic product of the following 78 1thN 3 H 0 A Br 3 Answer Section 1 67 19 MULTIPLE CHOICE Choose the one alternative that best completes the statement or answers the question 79 What is the major organic product obtained from the following sequence of reactions 79 O H soc12 CH3OH CHg c OH A O CH3 C O CH3 B CH2 C O CH3 C1 E O CH 3 O C H Answer A Section 16721 27 SHORT ANSWER so tht are the oroduets of the resetron of benzmc sero wrth thmnyl ehxorrdev Answer benzoylchlonde502gand HCI g 1572 Seetron 31 thch of the fonowrng reagents rs used In the followlng resetronv A PCI3 E 5125514 c HE D ClzP E CIQhu Answer A Seetron 15721 SHORT ANSWER 32 Answer 1 HNog H2504 c1 3 Name HCI cold CuCN Seetron 15721 COZH L SOC12A gt z NBOQCCHQC A Seetron 1572 Answer EA Answer y phosphorus ofATP ADP rs the oyoroouet of thrs resetron terrnrnsx Seetron 157 as wmh a the fullmng 5 pmme and mvmr c V c n HOOC COOH COOH COOH Dw COOH as Vvhzt 5 the m pmm a the faumng mm heaL 4 3 cioH ioH o o m OH OH A a n Answer a c m H20 an ur mum and pmwes We and denvihve upm heatxng A x e D a irbmyhie 2 anand Manda nswer A snow ANSWER laws the pH Shawlhe mm by mm m 5 farmed mbmt and C02 H20 2cm 89 Provide the major organic product of the following 89 gc5 H020 COZH W A Answer O O 0 Section 16723 90 An unknown compound C5H1002 gave the following proton NMR data 90 a doublet at 123 ppm 6H b singlet at 210 ppm 3H c septet at 498 ppm 1 H Propose a structure for the compound Answer CH3 C O b a CH o C CH3 CH3 S ection 99 31 1 wmh a the fullmng mmpmqas 5 immeth o Hioicrl3 I 1v 39 O 11 E4HZ 0 D1 gioH A x a n c m Answer 2 Which of the following compounds is a ketone CI x g O cg I O H O g CH 11 x 3 quotN Lg 0 D1 fag OH OJ v AI BH Answer B Section 1 77 1 3 What is the common name for the following compound 0 CH2 C H Cl A B chloroacetaldehyde B chloroaldehyde C oc chloroethanal D ot chloroacetaldehyde E 2 chloroethanal Answer D Section 1 77 1 2 O H CH a if V C OOH O C 111 D IV E V 3 4 Which of the following compounds is acetone A O CH3 C OH B 0 CH3 C CH3 C O CH3 C CH2CH3 D O H CH3 C H B 0 ll CH3 o C CH3 Answer B Section 1 7 7 1 5 What is the IUPAC name for the following compound 0 CH3CHCH2 C H Br A B bromobutyraldehyde B oc brornobutanal C 3 brornobutanone D 2 brornobutanal E 3 brornobutanal Answer E Section 1 7 7 1 4 a 6 Which of the following compounds is benzaldehyde CEHECII L FERN V39 x 930 LO Q R A I B H C III Answer D Section 1771 7 What is the TLJPAC name for the following compound 0 H CH3CCHCH2CHC1 CH3 CH3 A 5 chloro 35 dimethyl 2 pentanone B 2 chloro 4 methyl 5 hexanone C 1 chloro 13 dimethyl 4 pentanone D 5 chloro 3 rnethylhexanone E 5 chloro 3 methyl 2 hexanone Answer E Section 1 7 r 1 f 6 0 H CH C QOH D N E V 7 3 Which of the following is eyexonexanonev c m D W E v Seenon 17e 1 SHORT ANSWER 9 r r 9 nswer 4eme nyxe5epnenyxpeneonox Seenon 1m 10 m nswer zenyonoxyeeooxmecnyxe4eoo onone Seenon 1m 1 Provxde he IUPAC nome for the organ compound below 1 o o H OCHZCHg Answer ecnyxseoxooenconooce Seenon 1m 12 12 Provxde the IUPAC name for the organ compound below 0 er 3ee nyxe4eme nyxnexono1 1771 Seenon 13 Provroe the IUPAC name for the organre compound below 13 o OH Answer senydroxyeyexooeneanone Seenan 1771 14 Provroe the systematic name of the compound below 14 0 Cl Answer 2eenxoroesemecnyxneocanax Seenan 1771 15 Provroe the systematic name of the compound below 15 O Answer 2 VSemethyLAehepten e3rone Seenan 1771 H 4 Seenan 1772 17 Which carbonyl is more susceptible to nucleophilic attack that of cyclohexanone or 17 that of hexanal Provide two reasons for your choice Answer Hexanal The partial positive charge on the carbonyl carbon causes carbonyl compounds to be attacked by nucleophiles Because a hydrogen is electrone withdrawing relative to an alkyl group an aldehyde has a greater partial positive charge on its carbonyl carbon and is thus more susceptible to nucleophilic attack Steric factors also contribute to the greater reactivity of an aldehyde Because the hydrogen attached to the carbonyl carbon of an aldehyde is smaller than the alkyl group attached to the carbonyl carbon of a lltetone the carbonyl carbon of an aldehyde is more accessible to nucloephilic attacllt Section 1772 18 List the following carbonyl compounds in order of decreasing reactivity toward 18 nucleophiles ester acid chloride amide aldehyde lltetone Answer acid chloride gt aldehyde gt lltetone gt ester gt amide Section 177 2 MULTIPLE CHOICE Choose the one alternative that best I the or the l 19 Which of the following characterizes the reactions of aldehydes and ketones 19 A electrophilic substitution B electrophilic addition C nucleophilic addition free radical addition D nucleophilic acyl substitution Answer C Section 1773 20 Why do aldehydes undergo nucleophilic addition reactions while esters undergo nucleophilic 20 acyl substitution reactions A Once the nucleophile adds to an aldehyde the tetrahedral intermediate is too sterically hindered to eliminate one of the attached groups B The carbonyl carbon of an ester is more electrophilic than that of an aldehyde C Aldehydes are more sterically hindered than esters D The ester carbonyl carbon is sp3 hybridized while the aldehyde carbonyl carbon is sp2 hybridized E Once the nucleophile adds to an aldehyde neither Hr nor R7 can be elirninated since they are strongly basic Answer E Section 1773 21 What is the major product when CH32CHCH2CH2Br is subjected to the following reaction 21 sequence 1 Mg ether 2 C02 3 H30 A 4rmethy171 rpentanol B Zrmethy1727butanol C 4 Amethylpent anoic acid D 3 Amethyle 1 ebut anol Answer C Section 1774 22 Which of the following reactions can be used to prepare 3 rnethyl 3 hexanol OH CH3CH2CCH2CH2CH3 CH3 0 H 1 CH3CH2MgBr CH3CCH2CH2CH3 2 H3O 13 O H 1 CH3MgBr CH3CH2CCH2CH2CH3 9 2 H3O C O H l CH3CH2CH2MgBr CH3CCH2CH3 a 49 2 H30 D A and B E A B and c Answer E S ection 1 7 r4 23 What isare the major products of the following reaction 0 CH3MgBr HOCH2CH 9 A OMgBr HO CHZCH CEi3 B O HO CH2CCH3 HMgBr C 0 CH4 BngOCHZCH D O BngCHZCH CH3OH E O H CH3MgBr HOCHZCH 9 Answer C S ection 1 7 7 4 23 24 wmh a the fullmng mums an be used m prepare 9H CH3CH2C 7 o CchHzgiocHg I O 1 MgBr H H CHZCHZC 2 H30 i 1 CchHzMgBr 111 45 2 H30 A Equot mm D Em c E Mam c 2x255 ngmxd magma SHORT ANSWER Write the word or phrase that best completes each statement or answers the question 26 Complete the following reaction sequence by supplying the missing information 26 1 CH3OH gt CH3Br gt CH3CH20H 2 Answer 1 H PBr3 Mg H C H CH3OH CH3Br a CH3CH2OH ether 2 H3O Section 1 7 74 27 Give three different sets of reagents a carbonyl compound and a Grignard reagent 27 that could be used to prepare the following compound OH CH 3 c CH 2 CH3 CH3 Answer a O CH3CH2COCH3 and 2 CH3MgBr b O CH3CCH2CH3 and CH3MgBr c O H CH3CCH3 and CH3CH2MgBr S ection 1 7 74 28 What reagent can be used to convert benzophenone into triphenylmethanol 28 Answer PhMgBr followed by hydrolysis S ection 1 7 74 29 Propose a synthesis of 4 pheny1 2 butanol from 3 phenylpropanal 29 Answer 1 CH3MgBr 2 H30 S ection 1 7 74 11 33 34 prepare the s1eehe1 bexewv OH Answer benzsxdehyde 4 Seetrsn 17s Prevrde the major ergsnre preduet of the followxng Answer Seetrsn 1774 hexanal Answer 1 CH3CH2CH2CH2Er 5mm 3 H202 NsoH Seetrsn 1775 Prepese s synthesrs of 3ernethy1e4eheptyne3ee1frern Jebutyne Answer 1 NaNHz 2 cchocHch3 Seetrsn 1775 propose s sequenee of steps to eenvert prepyne to 4eheptsne1 Answer 1 NaNHz 2 cchmcmmo H2 exeess pt seetrsn 1775 35 Which of the following reactions is the best method for preparing acetaldehyde O H CH3C H A O H 1 DIBAH CH3CCl e 2 H3O B O H 1 LiAlH4 CH3COH 9 e 2 H3O C O H 1 LiAlH4 CH3CC1 e 2 H3O D O H 1 LiAlH4 CH3CNH2 9 e 2 H3O E O H 1 NaBH4 CH3COCH3 9 e 2 H3O Answer A Section 1 7 7 6 as What is the major product of the feuewmg reaction7 3 CN H NAME 4 7 2 H309 8 I N g e IV HZ a CEEN39H3 c m D W E v Sachem 174 37 thch A H2Pt a 1 LxAlH42 mm c 1 NeEH42 H30 E A E and c nsw E Seenen we the followlng 33 33 conversions V E carboxyhc and to es er Answer E Sachem 174 SHORT ANSWER treated thh DIEAH Answer CH32CHCH2CH2CHO 17e5 Sachem 40 Prevrde the major ergsnre preduet of the followxng 40 o 1 LrAlH4 CHZCHa N 1 H20 Answer NCHzCHa Seetrsn 177 41 Prevrde the major ergsnre preduets of the resetren below 41 o 1 NaBHr 2 H20 Answer seem 174 42 prmee the ms ergsnre preeuetrs er the reseth berew 42 1 LIAIH 2 MO 0 Answer Seetrsn 177 MULTIPLE CHOICE Choose the one alternative that best completes the statement or answers the question 43 Which of the following is the best method for preparing lactic acid from acetaldehyde 43 OH O CH3CHCOOH CH3CIH lactic acid acetaldehyde A CH3MgBr OH B C12 OH39 CH3OH C K1VInO4 OH D HCEN H30heat E C12 Mgether OH Answer D Section 1 7 7 7 44 Which of the sequences works best to accomplish the following conversion 44 OH CHO 2 MW A 1 NH3 H 2 H2 Pt B 1 H2NCH2MgBr 2 H3O C 1 NaNH2 2 H3O D 1 H2NNH2 H 2 H3O E 1 NaCN HCl 2 H2 Pt Answer E Section 1777 SHORT ANSWER Write the word or phrase that best completes each statement or answers the question 45 Provide the structure of the cyanohydrin that results when cyclopentanone reacts 45 with HCN Answer HO 3li Section 1 7 7 7 16 45 Prde the m WW prams a the martian beluw 1 New HCN 2 Ha H10 hea m Prde the m WW prams a the martian beluw 1 NaCN HCN 2 mpgc Answer DH ltCH2NH1 Presem at me and A mm Answer D 4 Wm the many gmp a a neutral lacuna 5 pm A Subsequent Weapme attatk m the msmung 5p andrtihlyzgd andth ea was 5 mu m mu under 1 award Weapme hunk bermAxes mm exmmpmu D the rememgspenes 1425 a pmem my the ibuve 50 thch A CH33CNH2 a CH3CH2CH2CH2NH2 e of the above nswer E Sachem 1775 51 thch of the following compounds is a hydrazone V 39 NHNHz N NN H N5 v NHZ 1 CH 111 NIliNH A x a n C m D xv swe D sham ma 52 What is the major organic product of the following reaction 0 CH3 C H HONH2 A CH3co NHOH 13 CH3CHOH ONH2 C CH3CHNHQCECE3 DH 3H D CH3CHOH NHOH E CH3C2NOH H Answer E Section 1 7 r 8 53 Which of the following is an enamine I N CH3 w J ENH HV a NCH3 V N N l 39 I CH3 j x V crg N IL A xCHB OH x A I B I C III D IV Answer B Section 1 7 r 8 EV 54 What is the major organ product of the following reaction7 0 0 CH3CH1NHCmCH3 7 IV Nfcz s Cz s 55 What is the major organ product of the following reaction7 0 Hz C zc zmz b39 Pt CECE on quot 0 N g NHC I lgC g 11 N532CH3 g NHCHZCHJ m A I a u c m nswer Sachem 1775 c m D W D W SHORT ANSWER 5e Pmmde the major organ products of the reaction below H m Answer H OVNW Sachem 1775 1 CHSCHZCHZNH H39 Cal 2 NaBHmAcpa 57 Provroe the major orgenre orooueqe of he reeenon below Seenon 1775 53 Provroe the structure of cyclohexanone oxxme Anew Seenon 1775 cyclohexanone s carbonyl group re protonated Answer Seenon 1775 Why this conversxon re eemeuy nrnoered by the oresenee of so rnuen and Answer Alvery low pH rnuen more of the ornrne re protonated end can no longer funcnon as e nucleophxle Seenon 1775 6 between benzaldehyde and methylamxne Answer 0 H g k 1amp6 H H L L g a sew 39 Ph H CH3 P u P1 k 11 mi ll ecu up IN AN 20 I gt H 20 LA f c z trimmer 39 P11 1 Ph 11 P H Seem 17a 62 62 between cyclohexanone and H2NOH Answer H W Sachem 1775 Answer Sachem 1775 0 cm 0 a CHngi 0 Y EH H CH b w a 3 9quot 37H 15 quot C ij CHEEHCH43 mfg H H ir u H 9 n 3 CH3CHH ch 39 3 cHg c 1 CHr 5 q 3 3 ca H3 9 CH3 c O CH C kroYc GHSCH ME 5 3 O HUqH CH m 3 as H iOH x CAOH QETQH NH b CH1NHlt 1 Z NH Sachem 1775 65 65 Clemmensen or s Womensnnerv Explain kc o 1 HDCHZCHgo u 93 A CHO 2 reduction 3 530 Answer Wolferxshner The and conditions of the Clemmensen would remove the peegeenns ensue esusms eeeuenen of use sxeenyee ss we Sesnsn 17ea as Provxde the major organ product of the following as CHZCHZN39H H can 0 Answer N Sesnsn 17a 67 Provxde the structure of he hydrate of cyclopentanone 67 Answer Sesnsn 173 the question MULTIPLE CHOICE Choose the one alternative that best I 39 the t t t or 68 The compound 68 O HOCH2CH2CH2CH2 CH can form a herniacetal by reacting with itself in solution What is the structure of this herniacetal H0 H HO OH HOYH OH I x 0 IV CI CI IZCHECHECH x OH J v CH3CH2CH0CH3 H A I B 11 C 111 D IV E V Answer B Section 17710 39 each t or the question SHORT ANSWER Write the word or phrase that best 69 Provide the structure of the diethyl acetal of butanal 69 Answer CH3CH2CH2CHOCH2CH32 Section 17710 70 70 Provide a detailed stepwise mechanism for the acid catalyzed reaction of 2 butanone with ethylene glycol HOCHZCHZOH to produce an acetal Answer 0 r H J3 xx ax V k xw r H H6 I H mansfer Arr 0 N 39CI xx 2 VKA quotxv EJ OH quotOH 39HgCl39 m m p 0 J l 0 39O H 0 gtlt A39 F H I M RV K39 x Section 1 7 7 10 71 H a the structure of m mam Answer 0 0 5m 1mm 72 mm 5 he mam mam of the following reachan39V o OH H exress 7 I O OH lt gt dial1 I 08 A E cjm D xv EV Sachem 17V 11 73 What sequence of reactions would best accomplish the following conversion D O O OH 0 ll CH3CCH2CH CH3CHCH2CH A NaBH4H30 B HOCHzCHonH NaBH4 HH20 C HzPt PCC D LiA1H4H30 E K1VInO4HO heat Answer B Section 17711 SHORT ANSWER Write the word or phrase that best 39 t t t t 1 each or 74 Propose a sequence of steps to carry out the following conversion 0 OH 32 L Iain wrx H P T x Xxx 393 Answer 1 HOCHzCHon H 2 NaNH2 3 CH3I 4 H3O 5 NaBH4 or LiAlH4 Section 17711 75 Propose a sequence of steps to carry out the following conversion 0 HO Kquot x K L 11 L 1 CHO v CHO Answer 1 HOCHzCHon H 2 CH3CH2CH2MgBr 3 H30 Section 1 7 r 1 1 27 the question 74 75 following alkene V gtCH calmj o I C g lc j OPCg 3 m lt gto CHICHJCHPC5Hlt3 0 u 391 chuchI mcohlg a u D n or m A x c m nswer D Sachem 17713 77 Which A CH3CH2CHPPh3 CH3CH2CH2CH2CHO a CH3CH2CH2CHFPh3 CH3CH2CH2CHO E CH3CH2CH2CH2MgEr CH3CH2CH2CHO nswer E Sachem 174 SHORT ANSWER 73 h both stereoxsomers 11 Ph H In Ph PC 4 CHZ Pll Answer Sachem 17V 13 E I u or m fromybmmobucane Answer 1 Ph3P 2 butylhthxum Sachem 1771 so Provxde the major organ products of the reaction below so 1 Ph3P Br 2 BuLI 3 3 pamanone Answer Sachem 17V 13 benzaldehyde TH H 139 TCH3 IV CH3 397 H OH H CH1 H OH V CH3 m DH CH3 A x a u c m D xv E v swer A Sachem 17V 14 SHORT ANSWER 32 y observed Whmh face of the carbonyl carbon 7 or 5 was attacked7 1 CH3cH2MgEr 0H 1 Ho o C112CH3 Answer enemy when Sachem 17V 1 0 5 CH A CH32CuL1H30 E cHaEr Hgo C CH3ErL1AlH4H3O D L1AlH4yCH3MgErH30 E CHgMgEr H30 Answer E Seem 17715 0 o 7 03 A L1AlH4yCH3MgErH30 E CH3Er L1A1H4 H30 C CH3MgEr Hgo D mummyme E CH3Er Hzo An we Seem 1115 as v p mum chemical shm of eppm a 20 ppm A 9 010 0 ppm E 4 045 ppm B Sachem 99 c 40 ppm D so ppm E 200 ppm SHORT ANSWER s7 3 C c3781 I Answer Compound 1 shows e on peak m me aldehyde at 27oo emel whue compound 11 shows e peek at 4330 Sachem 99 below c15H14O e mpxec at 2 1 ppm 2H p triplet at 24 ppm 2H e multiplet at 7 9 e 7 2 ppm 10H Answer 3 Kc Sachem 99 c emel for CH3 so c10H120 a triplet at 1 0 ppm 3H d multiplet at 7 2 ppm 5H Propose a structure for A Answer 1 c an a CHZCCH2CH1 Sachem 99 Answer cHscocl Ale r a Fnedelrcra s acylanon reaction Sachem 99
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